Reaktion #157197

Reaktionsgleichung

38c

N-Methoxy-N-methyl-6-phenylpicolinamide

3,4,5-trimethoxyphenylmagnesiumbromide

→

1c

(6-Phenylpyridin-2-yl)(3,4,5-trimethoxyphenyl)methanone

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with water
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   Trocknendried with MgSO4
4. 4
   SonstigeThe solvent was removed under reduced pressure
5. 5
   Sonstigeto yield a crude product, which
6. 6
   Sonstigewas purified by column chromatography

Vorschrift

To a solution of 38c (0.210 g, 0.86 mmoL) in 5 mL THF was added a THF solution of 3,4,5-trimethoxyphenylmagnesiumbromide (0.5 N, 3.5 mL, 1.73 mmol) at 0° C. The mixture was allowed to stir for 30 min and quenched with water, extracted with ethyl acetate and dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure 1c as white needle crystals (78%). 1H NMR (CDCl3) δ 8.10 (d, br, 2H), 8.02-8.00 (m, 1H), 7.97-7.96 (m, 2H), 7.66 (s, 2H), 7.49-7.43 (m, 3H), 3.97 (s, 3H), 3.89 (s, 6H); MS (ESI) m/z 372.6 (M+Na)+.

Quelle